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One-pot synthesis of α,β-unsaturated ketones from tert-butyldimethylsilyldibromomethane and two different aldehydes

✍ Scribed by Hiroshi Shinokubo; Koichiro Oshima; Kiitiro Utimoto

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 262 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73086-3

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✦ Synopsis

An addition of benzaldehyde to an ethereal solution of w-butyldimethylsilyldibromo methyllithium provided or-bromo-a-silyl ketone. Further treatment of the a-bmmoa-silyl ketone with butyllithium afforded enolate which provided g-hydroxya-silyl ketone upon treatment with aldehyde in ether. The enolate gave a,&unsaturated ketone or monosilyl ether of 2-acyl-1.5diol in THF instead of ether.

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